#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/37/2233778.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2233778
loop_
_publ_author_name
'Akerman, Matthew P.'
'Maher, Sarah J.'
_publ_section_title
;
 (E)-2,3-Bis[(E)-benzylideneamino]but-2-enedinitrile
;
_journal_coeditor_code           EZ2280
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o688
_journal_paper_doi               10.1107/S1600536812005363
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C18 H12 N4'
_chemical_formula_moiety         'C18 H12 N4'
_chemical_formula_sum            'C18 H12 N4'
_chemical_formula_weight         284.32
_chemical_name_systematic
;
(E)-2,3-Bis[(E)-benzylideneamino]but-2-enedinitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.96(5)
_cell_angle_beta                 91.67(5)
_cell_angle_gamma                102.97(5)
_cell_formula_units_Z            1
_cell_length_a                   6.389(4)
_cell_length_b                   7.608(5)
_cell_length_c                   8.311(5)
_cell_measurement_reflns_used    2824
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      3.3
_cell_volume                     380.6(4)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 2 CCD'
_diffrn_measurement_method       'ω scans at fixed θ angles'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2824
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         3.28
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_correction_T_min  0.9625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             148
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.894
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0717P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1166
_reflns_number_gt                964
_reflns_number_total             1498
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2280.cif
_cod_data_source_block           I
_cod_database_code               2233778
_cod_database_fobs_code          2233778
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 -0.8068(3) 0.8047(3) 0.9287(2) 0.0708(5) Uani d . 1 1
H H1 -0.9171 0.8241 0.9965 0.085 Uiso calc R 1 1
C C2 -0.7329(3) 0.9254(3) 0.8351(2) 0.0664(5) Uani d . 1 1
H H2 -0.7932 1.0265 0.8383 0.080 Uiso calc R 1 1
C C3 -0.5686(2) 0.8984(2) 0.7353(2) 0.0547(4) Uani d . 1 1
H H3 -0.5176 0.9818 0.6720 0.066 Uiso calc R 1 1
C C4 -0.7201(3) 0.6539(3) 0.9241(2) 0.0670(5) Uani d . 1 1
H H4 -0.7715 0.5720 0.9887 0.080 Uiso calc R 1 1
C C5 -0.5573(2) 0.6243(2) 0.82398(19) 0.0544(4) Uani d . 1 1
H H5 -0.4998 0.5215 0.8202 0.065 Uiso calc R 1 1
C C6 -0.4787(2) 0.74650(19) 0.72903(16) 0.0436(4) Uani d . 1 1
C C7 -0.3065(2) 0.72118(19) 0.62138(17) 0.0451(4) Uani d . 1 1
H H7 -0.2608 0.8070 0.5592 0.054 Uiso calc R 1 1
C C8 0.0179(2) 0.7027(2) 0.40742(18) 0.0469(4) Uani d . 1 1
C C9 -0.0504(2) 0.57010(17) 0.50538(16) 0.0399(3) Uani d . 1 1
N N1 0.0604(2) 0.81235(19) 0.33473(18) 0.0687(5) Uani d . 1 1
N N2 -0.21601(17) 0.58581(15) 0.60912(13) 0.0412(3) Uani d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle
C2 C1 C4 . 120.52(15)
C2 C1 H1 . 119.7
C4 C1 H1 . 119.7
C1 C2 C3 . 120.11(15)
C1 C2 H2 . 119.9
C3 C2 H2 . 119.9
C2 C3 C6 . 120.20(16)
C2 C3 H3 . 119.9
C6 C3 H3 . 119.9
C1 C4 C5 . 120.00(17)
C1 C4 H4 . 120.0
C5 C4 H4 . 120.0
C4 C5 C6 . 120.29(15)
C4 C5 H5 . 119.9
C6 C5 H5 . 119.9
C5 C6 C3 . 118.88(13)
C5 C6 C7 . 122.30(13)
C3 C6 C7 . 118.82(14)
N2 C7 C6 . 122.49(13)
N2 C7 H7 . 118.8
C6 C7 H7 . 118.8
N1 C8 C9 . 175.27(15)
C9 C9 N2 2_566 120.38(15)
C9 C9 C8 2_566 118.58(14)
N2 C9 C8 . 121.04(11)
C7 N2 C9 . 119.86(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.358(2)
C1 C4 . 1.375(2)
C1 H1 . 0.9300
C2 C3 . 1.377(2)
C2 H2 . 0.9300
C3 C6 . 1.392(2)
C3 H3 . 0.9300
C4 C5 . 1.375(2)
C4 H4 . 0.9300
C5 C6 . 1.381(2)
C5 H5 . 0.9300
C6 C7 . 1.4551(19)
C7 N2 . 1.2751(17)
C7 H7 . 0.9300
C8 N1 . 1.1340(17)
C8 C9 . 1.4456(19)
C9 C9 2_566 1.352(2)
C9 N2 . 1.3918(17)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion
C4 C1 C2 C3 . -0.5(3)
C1 C2 C3 C6 . 0.5(3)
C2 C1 C4 C5 . -0.1(3)
C1 C4 C5 C6 . 0.7(3)
C4 C5 C6 C3 . -0.6(2)
C4 C5 C6 C7 . 179.93(14)
C2 C3 C6 C5 . 0.1(2)
C2 C3 C6 C7 . 179.53(14)
C5 C6 C7 N2 . -0.7(2)
C3 C6 C7 N2 . 179.89(12)
C6 C7 N2 C9 . -179.29(12)
C9 C9 N2 C7 2_566 178.32(15)
C8 C9 N2 C7 . -1.5(2)
